JPH06104665B2 - Sulfonic acid group-containing perylene compound, method for producing the same and use thereof - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides compounds of the general formula I Wherein, A is -O -, = NR ¹ or = NR ² -SO ₃ ^- mean X ⁺ divalent residue, and B is = NR ² -SO ₃ ^- X ⁺ divalent residue A group, D is a chlorine- or bromine atom and, where n> 1, a combination thereof, and n is a number from 0 to 8; In, R ¹ is a hydrogen atom or an alkyl group having 1 to 30 carbon atoms, particularly an alkyl group having 1 to 18 carbon atoms, and particularly 1 to 1 carbon atoms.
4 alkyl groups, or unsubstituted or halogen atoms such as chlorine- or bromine atoms, sulfo groups, methyl-
Or an alkyl group having 1 to 4 carbon atoms such as an ethyl group,
An aryl group optionally substituted at one or more positions with an alkoxy group having 1 to 4 carbon atoms such as a methoxy- or ethoxy group or a phenylazo group, in particular a phenyl group, and R ² has 1 to 1 carbon atoms. 6 is a linear or branched alkylene group, especially an ethylene- or propylene group, X ⁺ is hydrogen ion H ⁺ or the 1st to 5th main group or the 1st or 2nd or 4th to 8th subgroup of the periodic table Equivalent to M ^{m +} / m of metal cation (where m is a number of 1, 2 or 3), for example Li ¹⁺ , Na ¹⁺ , K ¹⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Mn ²⁺ , Cu ²⁺ , Ni
²⁺ , Cd ²⁺ , Co ²⁺ , Zn ²⁺ , Fe ²⁺ , Al ³⁺ , Cr ³⁺ or Fe ³⁺ or defined as ammonium-ion N ⁺ R ³ R ⁴ R ⁵ R ⁶ , Provided that the substituents R ³ , R ⁴ , R ⁵ and R ⁶ attached to the quaternary nitrogen atom
Are independently of each other hydrogen atom or alkyl having 1 to 30 carbon atoms, alkenyl having 1 to 30 carbon atoms, cycloalkyl having 5 to 30 carbon atoms, unsubstituted or alkyl having 1 to 8 carbon atoms. substituted phenyl or (poly) alkyleneoxy group - _{^{[CH (R 7) -CH 2 -O-}} ) k -H
Wherein R ⁷ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and k is a number of 1 to 30; and
Alkyl-, alkenyl-, cycloalkyl-, phenyl or alkylphenyl groups identified as R ³ , R ⁴ , R ⁵ and / or R ⁶ are optionally further substituted with amino-, hydroxy- and / or carboxy groups. The substituents R ³ and R ⁴ may also be combined with a quaternary nitrogen atom to form a pyrrolidone-, imidazolidine-, hexamethyleneimine-, piperidine-, piperazine- or morpholine ring system. Well; or the substituents R ³ , R ⁴ and R ⁵ together with a quaternary nitrogen atom,
Pyrrole-, imidazole-, pyridine-, picoline-, pyrazine-, quinoline- or isoquinoline systems may be formed. ] A new and high-valued sulfonic acid group-containing perylene compound represented by the following formula: wherein n is 0 and both A and B are
The perylene compound is _{N-CH 2 CH 2 -SO 3} H are excluded - related.

In particular compounds Leaning interest of the present invention, A and B are the same, respectively = NR ² -SO ₃ ^- mean X ⁺ divalent residues as well as D and n are defined as described above, provided that the In residues A and B, R ² has the meanings identified above and X ⁺ is hydrogen ion H ⁺ or the equivalent of the chemical elements individually listed above M ^{m +} / m metal cation or ammonium-ion N ^+. R ³ R ⁴ R ⁵ R ⁶ with the substituent of the quaternary nitrogen atom
R ³ , R ₄ and R ⁵ are independently of each other a hydrogen atom or a hydroxyalkyl group having 2 to 3 carbon atoms and R ⁶ is alkyl having 1 to 30 carbon atoms, 1 to 30 carbon atoms
A compound of the general formula I which is one of the groups of the group alkenyl, hydroxyalkyl having 2 to 3 carbon atoms or cycloalkyl having 5 to 6 carbon atoms.

Of great value, A in formula I is -O-, = NR
¹ or _{= N-CH 2 -CH 2 -SO} 3 - X + is a divalent residue, B is _{= N-CH 2 -CH 2 -SO} 3 - X + is a divalent residue and n is the number 0, with the proviso that in said residues A and B R ¹ has the meanings identified above and X ⁺ is the cation H ⁺ or Ca ²⁺ / 2 or the ammonium-ion N ⁺ H ₃ R ⁶ Wherein R ⁶ is a sulfonic acid group-containing perylene compound of the invention of the type described immediately above.

The subject of this invention is also the process for the preparation of the abovementioned sulfonic acid group-containing perylene compounds having the chemical structure of the general formula I.
These novel compounds include perylene-3,4,9,10-tetracarboxylic acid-moni anhydride-monoalkali metal salt, especially monopotassium salt, perylene-3,4,9,10-tetracarboxylic acid-
Monoanhydride-monoimide, -N-monoalkyl- or -N-monoarylimide or perylene-3,4,9,10
A tetracarboxylic acid-dianhydride having the general formula II H ₂ NR ₂ —SO ₃ ^— X ⁺ (II) [wherein R ₂ and X ⁺ have the meanings given above. ] A sulfonic acid group-containing primary aliphatic amine represented by, for example, an aminoalkanesulfonic acid or a salt thereof, for example, taurine (2-aminoethanesulfonic acid) can be obtained by reacting with Condensation reaction of substances in aqueous solution, especially under alkaline pH conditions
Perform at a temperature in the range of ~ 180 ° C. In this case, it is expedient to use an excess of the amine of formula II. Isolation of the resulting process product of formula I from the reaction mixture is carried out by filtering its salt, which is subsequently converted to the corresponding free sulfonic acid by treatment with a strong mineral acid, for example sulfuric acid.

Instead of in an aqueous medium, the condensation reaction of both reaction components is carried out in a high-boiling inert organic solvent such as quinoline, imidazole, naphthalene, -chloronaphthalene, trichlorobenzene or phenol at a temperature of> 100 ° C., in particular 180 to twenty three
It may be carried out in the range of 0 ° C., optionally in the presence of a known catalyst (reaction accelerator), for example, sulfuric acid, phosphoric acid or zinc salt. According to this modified synthetic method the sulphonic acid group-containing perylene compound of formula I, which is formed as a salt, is preferably
Advantageously, it is optionally pre-diluted with an inert organic solvent, such as an aliphatic alcohol or an aliphatic ketone, under high temperatures such as in the range of 80 to 120 ° C., and then filtered off from the reaction mixture. is there. If desired, the separated sulphonate is then converted by hydrolysis in the customary manner to the free acid form.

According to the invention, when it is desired to prepare perylene compounds of the formula I which are asymmetrically substituted at the two imide nitrogen atoms, the two adjacent tetracarboxylic acids of the perylenes used as starting materials While utilizing the different reactivities of the structurally different derivatives with respect to the acid pair, optionally by reacting stepwise with the sulfonic acid group-containing amine of formula II, taking into account the amounts used as well as the reaction conditions. Or R ¹ -NH ₂ aliphatic-
Or aromatic primary one alkylene sulfonic acid group on the side of the amine imide nitrogen present a -R ² -SO ₃ ^- X ⁺ already having the formula I
Of perylenetetracarboxylic acid monoanhydride-monoimide.

The perylene compounds containing halogenated sulfonic acid groups of formula I with n> 0 are the corresponding galogenation products (> 0) of the perylene tetracarboxylic acid derivatives described above as starting compounds.
By condensation with sulphonic acid group-containing amines of the formula II or already prepared but halogen-free (n
= 0) obtained by subsequent halogenation of the process product of formula I.

Salts of perylene compounds containing sulphonic acid groups with X ⁺ ≠ H ⁺ are--as explained above--obtained already in the synthesis--or--if a particular cation X.sup. ⁺ Is considered--in this regard.
Preferably X ⁺ meaning a metal salt or an amine in the free acid matches of (X ⁺ = H ⁺⁾ are prepared separately by treating intentionally in aqueous solution.

DE-A-3,703,513 describes perylenetetracarboxylic acid arylene imides containing sulphonic acid groups which differ structurally from the compounds of the invention and are used as water-soluble fluorescent dyes. The water solubility of this dye is achieved by introducing sulfonic acid groups on both terminal residues of the dye. However, these compounds are not suitable for use as pigments or pigment dispersants.

Described in the appended claims, one or two anionic sulfonate - / sulfonate group -R ² -SO ₃ ^- Properties of a perylene compound of the formula I with X ⁺ is the case where a different imide nitrogen Can be adjusted in a wide range by specially selecting the existing substituent R ¹ or the number n of halogen atoms D of the polycyclic system and the cation X ⁺ . The profile of the properties required of each of these novel compounds for their respective purposes is
It must be directed by preliminary experiments and must be deliberately optimized. Thus, depending on the nature of the substituents and cations, compounds are obtained which are soluble in water and polar organic solvents, nonpolar organic solvents or synthetic resins. The compatibility of the process product in the medium in question can additionally be influenced by introducing hydrophobic or hydrophilic substituents or cations. Hydrophobic amine residues (long-chain alkylene groups) generally accelerate solubility in organic solvents and synthetic resins. Hydrophilic or water-soluble amines promote solubility in aqueous or polar systems.

According to the invention, it is also possible to obtain very sparingly soluble compounds of formula I by appropriate modification of the cation. This compound can already be used as a pigment by itself because of this property. Such a fact applies to monovalent and especially divalent or polyvalent metal cations.

The sulfonated perylene compounds of the present invention of formula I have been demonstrated as valuable colorants. Depending on the nature of the substituents and cations, they can be regarded as pigments, pigment dispersants or fluorescent dyes for this purpose. Halogenated sulphonated perylene compounds of this type dissolve as free sulphonic acid in their salt form as well as in aqueous and organic media. They are characterized by a high fluorescence intensity that can be achieved and a good fastness and can therefore be used in applications as fluorescent dyes for coloring aqueous or aqueous-organic media as well as liquid or solid organic substances.

Thus, the perylene compounds of the present invention are suitable for use in light collection systems and in analytical detection methods, in colored liquid crystal displays, to create low temperature light sources, for material testing, and for fine structure of semiconductor components. Can be used for research as well as for marking and communication purposes.

Liquid organic substances that can be dyed with such fluorescent dyes include, for example, alcohols, ketones, halogenated hydrocarbons,
Ethers, esters, aromatic- and aliphatic hydrocarbons,
There are nitrites, amines, nitro compounds, amides or mixtures thereof with one another as well as mixtures of these solvents with binders.

Solid organic substances which can be colored with fluorescent dyes of this type include synthetic resins and plastics such as amino resins, especially urea- and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenolic resins, polycarbonates. , Polyolefins such as polystyrene, polyvinyl chloride, polyethylene and polypropylene, polyacrylonitrile, polyacrylic esters, polyamides, polyurethanes or polyesters, which can be used on their own or in the form of mixtures or copolymers.

The readily soluble and sparingly soluble sulfonated perylene compounds are also, due to the influence of their anionic nature, high-performance dispersants for the preparation of pigment preparations. Preparations of this type have excellent color and flow properties.

Perylene-type alkaline earth metal salts of sulfonic acids,
Heavy metal salts or amine salts can be directly and advantageously utilized as pigments because of their poor solubility. They show very good color and flow properties.

Mixing the easily soluble or sparingly soluble sulfonated perylene compounds of the formula I as dispersants with basic pigments of the same or different chemical origin, for example azo-, quinacridone- and among others basic pigments of the perylene compound class. Alkaline earth metal salts, heavy metal salts and amine salts of sulphonic acid suitable for use as pigments due to their poor solubility are prepared by the preparation of high molecular weight natural or synthetic sources. It can be used outstandingly for pigmenting (coloring) organic substances.

Macromolecular organic substances which can be pigmented with pigment preparations prepared on the basis of the claimed sulphonic acid group-containing perylene compounds of the formula I or products of this type include, for example, cellulose ethers and -esters, for example Ethyl cellulose, nitrocellulose, cellulose acetate and cellulose butyrate, natural or synthetic resin,
For example polymerized or condensed resins such as amino resins, especially urea- and melamine-formaldehyde resins, alkyd resins, acrylic resins, phenolic resins, polycarbonates, polyolefins such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, poly. Acrylic esters, polyamides, polyurethanes or polyesters, rubbers, caseins, silicones and silicone resins, each alone or in a mixture with one another.

It does not matter here whether the polymeric organic compound is present in the form of a plastic composition, melt or spinning solution, lacquer, paint or printing ink. Depending on the intended use, it has proved to be advantageous to use the perylene compounds of the invention or the pigment preparations with which they are prepared as toners or in the form of formulations or dispersions. The claimed perylene compounds or pigment preparations derived therefrom are used in amounts of 1 to 10% by weight, based on the polymeric organic substance to be pigmented.

Particularly useful coating systems in this respect are baking coatings of the type alkyd / melamine resin or acrylic / melamine resin coatings as well as two-component coatings based on acrylic resins which can be crosslinked with polyisocyanates. Of the many printing inks that can be pigmented, mention can be made in particular of printing inks based on nitrocellulose.

The perylene compounds of the invention or the pigment preparations produced in cooperation with them can be easily and very finely dispersed in many application media. The dispersion has a high flocculation stability and exhibits excellent rheological properties even with high pigment loadings. This dispersion makes it possible to produce coatings and inks which have a good color strength, high gloss and high transparency with high fastness.

The perylene compounds of the invention or pigment preparations based on them are outstandingly suitable as colorants soluble in polymers for coloring moldable synthetic resins, in particular polyvinyl chloride, polyethylene and polypropylene. Colorings of good color strength and very good dispersibility are obtained.

In order to evaluate the properties of the products of the formula I according to the invention according to the invention according to the invention, or the pigment preparations which incorporate them, in coating systems, synthetic resin acids are among the many known systems. Alkyd- / Melamine Resin Paints (AM6) Based on Non-drying Akid Resins in Medium Oil and Phthalic Anhydride and Melamine Resins Etherified with Butanol and Containing Non-drying Alkyd Resins Based on Lysic Acid (Short Oil) And alkyd resin baking coatings based on non-aqueous dispersions (TSA-
NAD) was selected. In the examples below, these are A
Designated by the symbols M6 and TSA-NAD.

Fluidity of pulverized product after dispersion treatment (millimeter-based fluidity (mi
llbase rehorogy)] is evaluated by the following five scales: 5 Dilute solution 2 Slightly gelled 4 Liquid 1 Gelled 3 Viscous liquid The viscosity of Erichsen after diluting a pulverized product into a pigment-rich substance
It was evaluated with a Rossmann type viscosity spatula 301 type manufactured by the same company.

Gloss measurement at an angle of 20 ° according to DIN 67530 (ASTM D523)
Performed on casted molded films with a "multi-gloss" gloss measuring device from Byk-Mallinckrodt.

Test in polyvinyl chloride (PVC) at 120 ° C and
Performed at 160 ° C.

In the examples below, all parts are parts by weight and the percentages are percentages by weight of the substances mentioned. The type designations used to identify the pigments used in accordance with the invention and the CI numbers that direct them are Color Index, 3rd Edition,
1971 and addendum, 1975, 1982 and 1987.

Example 1 (reference example) 39.2 g of perylene-3,4,9,10-tetracarboxylic dianhydride are suspended in 1200 ml of water in an autoclave. 50 g of taurine and 26.4 g of potassium hydroxide (85% strength) are added to this suspension, after which the mixture is stirred at 150 ° C. for 5 hours. After cooling to 25 ° C., the reaction product which has precipitated is filtered off with suction, washed with water until neutral and
Dry at ℃.

For conversion to the acid state, the compound of formula III thus isolated as the dipotassium salt, is now initially reacted at 25 ° C. with 1400 g of
Introduce and dissolve in 100% strength sulfuric acid. Thereafter, a further 930 g of 50% strength sulfuric acid are added dropwise to this solution. At that time, the temperature may rise to 80 ° C. Then cool to 25 ° C. The liberated sulphonic acid is then filtered on a glass suction filter, after-washed with 80% strength sulfuric acid, washed with sulfate-free by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure. To do.

Yield: 59.0 g of the compound of formula III above (containing 6.2% of water of crystallization), 55.3 g of 100% concentration (= theoretical value)
91.3%).

Analysis: C ₂₈ H ₁₈ N ₂ S ₂ O ₁₀ (6.2% H ₂ O taken into account) Calculated: C 55.4%; H 3.0%; N 4.6%; S 10.6% Measured: C 55.5%; H 2.8%; N 4.7%; S 10.1% ¹ H-NMR-spectrum in D ₂ SO ₄ : shift position ( ¹ H) (doublet 8.77; 8.70); 4.68; 3.64 Example 1a European Patent 0,088,392 19.2 g CI Pigment Red 179 (No. 71130) of the perylene-type prepared without the addition of a surfactant in the same manner as described in Example 1 of the publication, 0.8 g as pigment dispersant. Is mixed with a perylene compound of formula III

A pigment preparation is obtained which, when tested with the TSA-NAD-paint, gives clear, bright and very dark high-gloss pure coatings. This metallic paint has a very good strength and is very pure. The product has a mill base fluidity (15% strength) rating of 5. In contrast, without the pigment dispersant, the color obtained with the colorant is more opaque and less deep in color. In this case, the mill base fluidity is a rating of 1.

Example 1b Perylene-type 17.6 g CI Pigment Red 179 (No. 7) prepared in the same manner as the formulation of Example 1 of EP 0,088,392 without the addition of a surfactant.
1130) is mixed with 2.4 g of perylene compound of formula III as pigment dispersant.

A pigment preparation is obtained which, when tested with the TSA-NAD-paint, gives clear, bright and very dark high-gloss pure coatings. The color strength and gloss of this coating are greater than those obtained according to Example 1a. This metallic paint is very dark and very pure. The mill-base fluidity (15% strength) of this product is rated 4-5 in this case. In contrast, without the pigment dispersant, the color obtained with the colorant is more opaque and less deep in color. In this case, the mill base fluidity (15% concentration) is rated 1.

Example 1c 10 g of the perylene compound of the formula III are introduced into 150 ml of water and dissolved. Then a solution consisting of 10 g of ethanol and 1 g of oleic acid monoethanolamide is added and the mixture is boiled under heating. In addition, a solution consisting of 10 g of calcium chloride (without water) and 200 ml of water is added dropwise during 10 minutes at boiling temperature. After stirring for a further 3 hours at boiling temperature, the reaction product which has precipitated is then filtered off with suction, washed free of chloride with water and dried at 80 ° C. TSA-
10.8 g of pigment (as Ca-salt) are obtained which gives a clear, high-gloss maroon coating in NAD-paint. The mill base fluidity (15% strength) of this product is a rating of 5.

Example 1d 10 g of the perylene compound of the formula III are introduced into 150 ml of water and dissolved. Then a solution consisting of 20 g of ethanol and 2 g of oleic acid monoethanolamide is added and the mixture is boiled under heating. A solution consisting of 10 g of nickel sulphate hexahydrate and 200 ml of water is added dropwise, this time over 10 minutes at boiling temperature. After stirring for a further 3 hours at boiling temperature, the reaction product which has precipitated is then filtered off with suction, washed free of chloride with water and dried at 80 ° C. TSA-
12.7 g of pigment (as Ni-salt) are obtained which gives a clear, high-gloss maroon coating in NAD-paint. The mill base fluidity (15% strength) of this product is a rating of 5.

Example 1e 15 g of the perylene compound of the formula III are introduced into 150 ml of water and dissolved. A solution consisting in turn of 15.5 g of abiethylamine and 50 ml of ethanol is added dropwise at the boiling temperature during 15 minutes. After stirring for a further 1 hour at boiling temperature, the reaction product which has precipitated is filtered off with suction, washed with water and dried at 80 ° C. 28.6 g of pigment (as abiethylammonium salt) are obtained which in TSA-NAD-paint give rise to a highly transparent, high-gloss scarlet-colored coating. The mill base fluidity (15% strength) of this product is a rating of 5. There is no problem with the overcoat fastness.

Example 1f 30 g of perylene-3, prepared as a crude pigment as described in Example 1 of German Patent Application Publication No. 1,067,157,
4,9,10-Tetracarboxylic acid-N, N '-(3', 5'-dimethylphenylimide) was used as a magnetic sphere (diameter
12 mm) introduced into a 1.4 liter stainless steel container filled with 1400 g and used as initial reactant. In addition to this mixture 90 g sodium sulfate (water-free), 0.7 g
Of stearylamine and 0.75 g of a perylene compound of the formula III as a pigment dispersant are added and this mixture is then mixed in a vibrating mill [Vibratom ™, manufacturer: Siebtechnik.
Crush on Muehlheim) with shaking for 8 hours. The resulting grind is then screened from the grind and stirred for 1 hour at 90 ° C. while being treated with hot water. The process product is then filtered off with suction, washed with water until free of sulfate and dried at 80 ° C. Perylene-type C.
Based on I. Pigment Red 149 (No.71137) 28.
6 g of pigment preparation are obtained. The product is tested in PVC and gives a pure color which is fast, transparent, bright and dark. In contrast, the pigment prepared without the addition of the dispersant of formula III gives an opaque dark blue color.

Example 1g 30 g of perylene-3,4,9,10-tetracarboxylic acid-diimide with a bromine content of 25.45%, prepared as in the formulation of Example 9 of EP 0,039,912, as ground material 1400 g of Cylpebs (from Corundum: diameter 12 mm; manufacturer Groh GmbH, Hof) are introduced into a 1 liter plastic container and used as initial reactant. In addition to this mixture 3g as a pigment dispersant
Of perylene compound of formula III and 3 g of stearylamine are added. The mixture is then finely ground for 12 hours with shaking on a vibrating mill (as in Example 1f), then the ground material is separated from the ground body by sieving. 31 g of the above ground product are then introduced into 340 ml of N-methylpyrrolidone, heated to 50 ° C. and post-stirred at this temperature for 3 hours. Then add 200 ml of water,
The reaction product is suction filtered, washed free of N-methylpyrrolidone by treatment with water and dried at 80 ° C. 29.5 g of pigment preparation based on brominated perylene-3,4,9,10-tetracarboxylic acid-diimide are obtained. When the TSA-NAD-paint is pigmented with the product, a clear, bright and pure coating is obtained. In contrast, without the addition of the dispersant of formula III, the pigmented coating is opaque, dark and weak in color. Liquidity is comparable in both cases. Nitrocellulose-based gravure printing gives very clear, deep and pure colours with the abovementioned preparations. Without the addition of the dispersant of formula III, the coloration in this product is opaque and hazy with a dark blue color.

Example 2 1200 ml of water are initially introduced into the autoclave and 37.6 g of taurine are dissolved therein. A pH value of 9.5 is achieved in this solution by further addition of 12.6 g of potassium hydroxide (85% strength). Then in this initial mixture 3
9.1 g of perylene-3,4,9,10-tetracarboxylic acid monoanhydride-monoimide are introduced and the mixture is then heated to 150 ° C.
Stir for 3 hours. After cooling to 25 ° C., the reaction product which occurs as K salt is filtered off with suction, washed with saturated potassium chloride solution until neutral and dried at 80 ° C.

The residue obtained is in turn first introduced into 1300 g of 100% strength sulfuric acid at 25 ° C. and dissolved. Then add 1070g to this solution.
50% strength sulfuric acid may be added dropwise, at which time the temperature may rise to 80 ° C. Then cool to 25 ° C. The sulfonic acid thus liberated is filtered on a glass suction filter, after-washed with 78% strength sulfuric acid, washed with sulfate-free by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure. .

Yield: 38.4 g of the compound represented by the above formula IV (containing 4.6% of water of crystallization), 36.6 g at 100% concentration (= 7 of the theoretical value).
3.5%).

Analysis: C ₂₆ H ₁₄ N ₂ SO ₇ (4.6% H ₂ O taken into account) Calculated: C 62.7%; H 2.8%; N 5.6%; S 6.4% Measured: C 63.3%; H 2.6 %; N 5.7%; S 6.1% Example 3 1200 ml of water are initially introduced into the autoclave and 50.1 g of taurine are dissolved therein. A pH value of 9.6 is achieved in this solution by further addition of 26.4 g of potassium hydroxide (85% strength). Then add 4 to this initial mixture.
0.5 g of perylene-3,4,9,10-tetracarboxylic acid monoanhydride-monomethylimide were introduced and then this mixture was added to
Stir at 150 ° C. for 3 hours. After cooling to 25 ° C., the reaction product, which occurs as the K salt, is filtered off with suction, washed with water and dried at 80 ° C. The residue obtained is in turn first introduced at 25 ° C. into 1000 g of 100% strength sulfuric acid and dissolved. Thereafter, a further 850 g of 50% strength sulfuric acid may be added dropwise to this solution, with the temperature rising to 80 ° C. Then cool to 25 ° C. The sulfonic acid thus liberated is filtered on a glass suction filter, after-washed with 78% strength sulfuric acid, washed free of sulphate by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure. .

Yield: 44.9 g of the compound represented by the above formula V (containing 1.9% of water of crystallization), 44.0 g at 100% concentration (= theoretical value of 8)
5.9%).

Analysis: C ₂₇ H ₁₆ N ₂ SO ₇ (1.9% H ₂ O taken into account) Calculated: C 63.3%; H 3.1%; N 5.5%; S 6.3% Measured: C 63.0%; H 3.4 %; N 5.4%; S 6.3% Examples 3a to 3j Perylene compounds of formula V are added as pigment dispersants to various pigments in various amounts in a series of experiments, mechanically mixed and obtained in this case. The pigment preparations are run in TSA / NAD-paint or AM6-paint for each base pigment. The application characteristic results obtained in this case are summarized below: Example 4 15.2 g of perylene-3,4,9,10-tetracarboxylic acid of formula III-N, N'-bis-prepared according to example 1 (reference example)
(2'-sulfoethyl imide was stirred at 25 ° C with 45
Introduce and dissolve in 0 g of 100% strength sulfuric acid. Then in this solution
Add 6.0 g of bromine and 0.2 g of iodine. The brominated mixture is then stirred at 125 ° C. for a further 6 hours, cooled to 25 ° C. and 500 g of 30% strength sulfuric acid are added dropwise at this temperature. The reaction product formed in this case is suction filtered on a glass suction filter, after-washed with 60% strength sulfuric acid, washed free of sulfate by treatment with 31% hydrochloric acid and at 80 ° C. under reduced pressure. dry.

Yield: 17.7 g of the compound represented by the above formula VI (containing 4.5% of water of crystallization), 16.9 g at 100% concentration (= theoretical value of 8
7.8%).

Analysis: C ₂₈ H _15.3 N ₂ S ₂ O _2.7 (4.5% H ₂ O taken into account) Calculated: C 40.7%; H 1.9%; N 3.3%; Br 26.4%; S 6.8% Measured: C 41.0%; H 1.9%; N 3.4%; Br 26.3%; S 7.8% When testing the product by dipping coloring of paper, a deep reddish colouration is obtained. The color of the nitrocellulose paint is deep red and fluorescent.

Example 5 31.4 g of perylene-3,4,9,10-tetracarboxylic acid of formula III-N, N'-bis-prepared according to example 1 (reference example)
(2'-sulfoethylimide was added to 402 g of 100% with stirring.
It is introduced into concentrated sulfuric acid and dissolved. After adding 0.6 g of sodium iodide to this solution, 70 g of chlorine was introduced at 20-25 ° C. for 12 hours, and 0.6 g of iodide was added at intervals of 3 hours. Add sodium. Then 560 g of 20% strength sulfuric acid are added dropwise to the chlorinated mixture at 20 ° -25 °. The reaction product which precipitates in this case is filtered on a glass suction filter, post-washed with 50% strength sulfuric acid, washed free of sulphate by treatment with 31% hydrochloric acid and at 80 ° C. under reduced pressure. dry.

Yield: 34.3 g of the compound represented by the above formula VII (containing 3.0% of water of crystallization), 33.3 g at 100% concentration (= theoretical value)
86.8%).

Analysis: C ₂₈ H _12.7 N ₂ S ₂ O ₁₀ Cl _5.3 (3.0% H ₂ O is taken into account) Calculated value: C 42.6%; H 1.6%; N 3.6%; Br 23.9%; S 8.1% measurement Values: C 42.4%; H 2.3%; N 3.1%; Br 23.9%; S 7.9% When the product is tested with dip coloring of paper, an orange-colored deep colouration is obtained. The color of the Nitricellulose paint is orange-colored and fluorescent.

Example 6 In a stirred vessel is first introduced 1200 ml of water and into it 101 g of taurine and 52.8 g of sodium hydroxide (85
% Concentration). The resulting solution is cooled to 0-5 ° C. and at this temperature 90.1 g of perylene-3,4,9,10-tetracarboxylic acid monoanhydride-monopotassium salt are introduced, then the mixture is mixed first. 2 hours at 20-25 ° C and then 90-95 ° C
Stir for another 3 hours. This reaction mixture is then added to 20 ~
Cool to 25 ° C., filter it with suction and filter the filter residue to 10
Wash with 0 ml water. 125 g of methanol and 300 g of potassium acetate (without water) are then added to the filtrate obtained, after which the liquid is stirred for 2 hours at 20-25 ° C. The reaction product which precipitates in this case is filtered off with suction, washed afterwards with an aqueous methanolic solution of 18% potassium acetate and 6% methanol and dried at 80 ° C.

The compound of formula VIII, which is isolated as the tripotassium salt, is now
At 20 to 25 ° C, 1230 g of sulfuric acid monohydrate is first introduced and dissolved. A further 820 g of 50% strength sulfuric acid may then be added dropwise to this solution, with the temperature rising to 80.degree. After cooling to 25 ° C. in advance, the sulfonic acid thus released is filtered with a glass suction filter and then washed with 80% sulfuric acid.
It is washed free of sulphate by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure.

Yield: 71.2 g of the compound represented by the above formula VIII (containing 6.1% of water of crystallization), 66.9 g at 100% concentration (= theoretical value)
66.7%).

Analysis: C ₂₆ H ₁₃ NSO ₈ (6.1% H ₂ O taken into account) Calculated: C 62.5%; H 2.6%; N 2.8%; S 6.4% Measured: C 63.2%; H 2.6%; N 2.8%; S 6.3% Example 7 9.8 g of perylene-3,4,9,10-tetracarboxylic acid-dianhydride are suspended in 290 ml of water in an autoclave. 13.9 g of 3-aminopropanesulfonic acid and
6.6 g of potassium hydroxide (85% strength) are added, then the mixture is stirred at 150 ° C. for 5 hours. After cooling to 25 ° C., a further 50 g of potassium chloride are introduced, the reaction product which precipitates is filtered off with suction, washed with 20% strength potassium chloride solution and dried at 80 ° C.

For conversion to the acid form, the compound of formula IX, isolated as the dipotassium salt, is first introduced at 25 ° C. into 300 g of 100% strength sulfuric acid and dissolved. Then add another 200 g in this solution
50% strength sulfuric acid may be added dropwise, with the temperature rising to 80 ° C. Then it is cooled to 25 ° C., the free sulphonic acid is then suction filtered on a glass filter, washed again with 80% strength sulfuric acid, washed with 31% hydrochloric acid until free from sulphate and reduced pressure. Dry at 80 ° C.

Yield: 14.9 g of the compound represented by the above formula IX (containing 5.4% water of crystallization), 14.1 g at 100% concentration (= 8 theoretical values)
Equivalent to 9.0%).

Analysis: C ₃₀ H ₂₂ N ₂ S ₂ O ₁₀ (5.4% H ₂ O is considered) Calculated: C 56.8%; H 3.5%; N 4.4%; S 10.1% Measured: C 56.9%; H 3.5%; N 4.2%; S 9.9% Example 8 50 ml of quinoline are initially introduced into a stirred vessel and then 4.99 g of perylene-3,4,9,10-tetracarboxylic acid-monoanhydride-N- of formula VIII prepared according to Example 6 are prepared.
Mono- (2'-sulfoethylimide) (93.9%) and
4.92 g of 4-methoxyaniline and 0.5 g of zinc acetate dihydrate are introduced successively. Then the reaction mixture is added to 19
Heat to 0 ° C. and stir at this temperature for 8 hours. Then 120
The reaction product, which is cooled to 0 ° C and which precipitates as the Zn-salt, is suction filtered at this temperature, after-washed with quinoline and methanol and dried at 80 ° C. The dried residue is now at 25 ° C
It is introduced into 65 g of 50% strength sulfuric acid and then stirred at 25 ° C. for 5 hours. The sulfonic acid thus liberated is then filtered on a glass suction filter, washed free of sulphate by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure.

Yield: 5.79 g of a compound represented by the above formula X (containing 4.3% of water of crystallization), 5.54 g at 100% concentration (= 9 of the theoretical value)
7.9%).

Analysis: C ₃₃ H ₂₀ N ₂ SO ₈ (4.3% H ₂ O taken into account) Calculated: C 65.6%; H 3.3%; N 4.6%; S 5.3% Measured: C 64.9%; H 3.2 %; N 4.6%; S 5.3% Example 9 R = C ₁₄ ~C ₁₈ - alkyl (mixture of natural) were introduced into the stirred vessel quinoline 50ml initially and then perylene of formula VIII of 4.99g prepared according to Example 6 3,4, 9,10-Tetracarboxylic acid-monoanhydride-N-
Mono- (2'-sulfoethylimide) (93.9%) and
21.6 g of C ₁₄ -C ₁₈ -alkylamine (natural mixture) and 0.5 g of zinc acetate dihydrate are introduced successively. Thereafter the reaction mixture is heated to 190 ° C. and at this temperature 8
Stir for hours. It is then cooled to 120 ° C. and the reaction product which precipitates as the Zn salt is suction filtered at this temperature, after-washed with quinoline and methanol and dried at 80 ° C. The dried residue is then initially introduced into 80 g of 50% strength sulfuric acid at 25 ° C. and dissolved. A further 52 g of 50% strength sulfuric acid are then added dropwise to this solution, with the temperature rising to 80.degree. After pre-cooling the reaction mixture to 25 ° C,
l Pour into water. The product which precipitates in this case is filtered off with suction and washed with water until free of sulphate. The moist compressed cake obtained is then introduced into a mixture of 100 ml of ethanol and 5.6 g of hydrochloric acid (31% strength) and stirred for 1 hour at boiling temperature. Finally,
The sulfonic acid thus liberated is filtered on a glass suction filter, washed with ethanol and dried at 80 ° C.

Yield: 6.80 g of the compound of formula XI above (containing 0.53% water of crystallization), corresponding to 6.76 g of dry product.

Analysis: Found H ₂ O are considered of 0.53: C 71.7%; H 7.9 %; N 4.1%; S 3.8% Example 10 50 ml of quinoline are initially introduced into a stirred vessel and then 4.99 g of perylene-3,4,9,10-tetracarboxylic acid-monoanhydride-N- of formula VIII prepared according to Example 6 are prepared.
Mono- (2'-sulfoethylimide) (93.9%) and
6.92 g of metanilic acid and 0.5 g of zinc acetate dihydrate are introduced one after the other. Thereafter the reaction mixture is heated to 190 ° C. and stirred at this temperature for 8 hours. Then it is cooled to 120 ° C., the reaction product which precipitates as the Zn salt is suction filtered at this temperature, after-washed with quinoline and methanol and
Dry at ℃.

The dried residue is introduced at this time into 86 g of 50% strength sulfuric acid at 25 ° C. and then stirred at 25 ° C. for 4 hours. The sulfonic acid thus liberated is then filtered on a glass suction filter, washed free of sulphate by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure.

Yield: 6.26 g of compound of formula XII above (containing 4.4% water of crystallization), 5.98 g at 100% concentration (= theoretical value)
97.2%).

Analysis: C ₃₂ H ₁₈ N ₂ S ₂ O ₁₀ (4.4% H ₂ O is considered) Calculated: C 58.7%; H 2.8%; N 4.3%; S 9.8% Measured: C 57.2%; H 3.1%; N 4.3%; S 9.3% Example 11 In a stirred vessel 50 ml of control pyridine, 4.99 g of perylene-3,4,9,10-tetracarboxylic acid of formula VIII-monoanhydride-N-mono- (2'-, prepared according to Example 6 Sulfoethylimide) (93.9%) and 0.5 g of zinc acetate dihydrate are introduced successively. The reaction mixture is then added to 20
Heat to 5-210 ° C. and stir at this temperature for 8 hours. It is then cooled to 25 ° C. and the reaction product which precipitates as the Zn-salt is filtered off with suction, after-washed with control pyridine and methanol and dried at 80 ° C.

The dried residue is then introduced into 63 g of 50% strength sulfuric acid at 25 ° C. and then stirred at 25 ° C. for 1 hour. The sulfonic acid thus liberated is then filtered on a glass suction filter, washed free of sulphate by treatment with 31% strength hydrochloric acid and dried at 80 ° C. under reduced pressure.

Yield: 5.75 g of the compound of formula XIII above (containing 3.1% water of crystallization), 5.57 g at 100% concentration (= theoretical value)
98.4%).

Analysis: C ₃₄ H ₂₂ N ₂ O ₇ S (3.1% H ₂ O taken into account) Calculated: C 67.8%; H 3.7%; N 4.7%; S 5.3% Measured: C 58.2%; H 3.8%; N 5.1%; S 5.1% The present invention relates to a sulfonic acid group-containing perylene compound according to the claims, a method for producing the same, and uses thereof, but also includes the following as embodiments: 1. Claims In the general formula I described in item 1, A and B are the same, each represents a divalent residue of NR ² —SO ₃ ^— X ⁺ , and D and n are the same as in claim 1. Provided that in the above residues A and B R ² is ethylene or propylene and X ⁺ is hydrogen ion H ⁺ or as in claim 1 Li ¹⁺ , Na ¹⁺ , K ^{1 +} , Mg ²⁺ , Ca
²⁺ , Sr ²⁺ , Ba ²⁺ , Mn ²⁺ , Cu ²⁺ , Ni ²⁺ , Cd ²⁺ , Co ²⁺ , Zn ²⁺ , Fe ²⁺ , Al
³⁺ , Cr ³⁺ and Fe ³⁺ in the equivalent (M ^{m +} / m) metal cation or ammonium-ion N ⁺ R ³ R ⁴ R ⁵ R ⁶ with the quaternary nitrogen atom The substituents R ³ , R ⁴ and R ⁵ are each independently of the other hydrogen atom or hydroxyalkyl group having 2 to 3 carbon atoms and R ⁶ is 1 to 1 carbon atom.
30 alkyls, 1 to 30 carbons alkenyls, 2 to 3 carbons hydroxyalkyls and 5 carbons
The perylene compound containing a sulfonic acid group according to claim 1, which is one of groups in the group of 6 cycloalkyls.

2. In the general formula I according to claim 1, A is —O— or NR ¹
Of a bivalent residue, B is = NR ² -SO ₃ ^- mean X ⁺ divalent residues and D and n are similarly defined as in claim 1, provided that the residues A And in B, R ¹ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, or is unsubstituted or substituted with a chlorine atom, a sulfo group, a bromine atom, a methyl group, an ethyl group, a methoxy- and / or an ethoxy group. Optionally a phenyl group, R ² is an ethylene- or propylene group and X ⁺ is a hydrogen ion H ⁺
Or as in claim 1, Li ¹⁺ , Na ¹⁺ , K ¹⁺ , M
g ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Mn ²⁺ , Cu ²⁺ , Ni ²⁺ , Cd ²⁺ , Co ²⁺ , Zn ²⁺ , F
^{Equivalent of} the group consisting of e ²⁺ , Al ³⁺ , Cr ³⁺ and Fe ³⁺ (M ^{m +} / m)
Metal cation or ammonium-ion N ⁺ R ³ R ⁴ R ⁵ R ⁶
Wherein the substituents R ³ , R ⁴ and R ^{5 on} the quaternary nitrogen atom are each independently of one another a hydrogen atom or a carbon number of 2 to
A hydroxyalkyl group of 3 and R ⁶ is a group of alkyl having 1 to 30 carbon atoms, alkenyl having 1 to 30 carbon atoms, hydroxyalkyl having 2 to 3 carbon atoms or cycloalkyl having 5 to 6 carbon atoms. It is one of the groups in. The sulfonic acid group-containing perylene compound according to claim 1.

3. In the general formula I according to claim 1 or any one of the above 1 or 2, A is -O- or = NR ¹ or = N-CH ₂ -CH ₂
-SO ₃ ^- X ⁺ is a divalent residue, B is _{= N-CH 2 -CH 2 -SO} 3 - X +
Is a divalent residue of n and n is 0, provided that in the above residues A and B, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X ⁺ is a cation H ^+. Or Ca ⁺² / 2 or ammonium-ion N ⁺ H ₃ R ⁶ , wherein R ⁶ is defined as in 1 or 2 above, or any one of 1 or 2 above. The sulfonic acid group-containing perylene compound according to.

4. The reaction product of formula I obtained in salt form as a sulfonate is converted to the corresponding free sulfonic acid of formula I by treatment with strong mineral acid, preferably after intermediate isolation. Or the method described in 3.

5. A pigment dispersant for producing a pigment preparation according to claim 4, wherein the basic pigment of the pigment preparation is a perylene compound or a derivative thereof which is the basis of the dispersant used.

6. A pigment dispersant for producing a pigment preparation according to claim 4, wherein the basic pigment of the pigment preparation is derived from a different type of compound than the dispersant used.

7. A coloring agent for pigmenting a polymeric organic material of natural or synthetic origin in the form of a plastic composition, melt, spinning solution, lacquer, paint or printing ink. Pigment preparation of paragraph 6.

8. Use of the easily soluble sulfonic acid group-containing perylene compound of the general formula I according to claim 1 or any one of claims 1 to 3 as a fluorescent dye.

9. Fluorescent paint according to claim 12 for coloring aqueous- or aqueous-organic media as well as liquid or solid organic substances.

10. A sparingly soluble perylene compound of the general formula I as defined in any one or more of claims 1 to 4, in particular as a colorant for pigmenting high molecular organic substances of natural or synthetic origin. Uses for salts of divalent or polyvalent metal cations.

Claims (8)

[Claims] 1. A general formula I Wherein, A is -O -, = NR ¹ or = NR ² -SO ₃ ^- mean X ⁺ divalent residue, and B is = NR ² -SO ₃ ^- X ⁺ divalent residue A group, D is a chlorine- or bromine atom and optionally a combination thereof when n> 1, and n is 0-8; provided that, in the above residues A and B, R ¹ represents a hydrogen atom or an alkyl group having 1 to 30 carbon atoms, or an unsubstituted or halogen atom, a sulfo group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or phenylazo. Is an aryl group which may be substituted at one or more positions with R ² , R ² is a linear or branched alkylene group having 1 to 6 carbon atoms, X ⁺ is a hydrogen ion H ⁺ or Equivalent M ^{m +} / m metal cations of the 1st to 5th main groups or the 1st or 2nd or 4th to 8th subgroups (Where m is a number of 1, 2 or 3) or ammonium-ion N ⁺ R ³ R ⁴ R ⁵ R ⁶ provided that the substituent R ³ is attached to the quaternary nitrogen atom. , R ⁴ , R ⁵ and R ⁶
Are hydrogen atoms or carbon atoms 1 independently of each other
~ 30 alkyl, alkenyl having 1 to 30 carbon atoms, cycloalkyl having 5 to 30 carbon atoms, phenyl or (poly) alkyleneoxy group which is unsubstituted or substituted by alkyl having 1 to 8 carbon atoms- [ _{^{CH (R 7) -CH 2 -O-}} ) k -H ( wherein, R ⁷ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and k is a number from 1 to 30) and R ³ , R
^The alkyl-, alkenyl-, cycloalkyl-, phenyl- or alkylphenyl groups identified as ⁴ , R ⁵ and / or R ⁶ are optionally further substituted with amino-, hydroxy- and / or carboxy groups. Or the substituents R ³ and R ⁴ together with the quaternary nitrogen atom may form a pyrrolidone-, imidazolidine-, hexamethyleneimine-, piperidine-, piperazine- or morpholine ring; or The groups R ³ , R ⁴ and R ⁵ together with a quaternary nitrogen atom,
A pyrrole-, imidazole-, pyridine-, picoline-, pyrazine-, quinoline- or isoquinoline ring may be formed. Sulfonic acid group-containing a perylene compound represented by] - where n is two values a and A and B 0 = N-CH the perylene compound is ₂ CH ₂ -SO ₃ H are excluded -. 2. A and B in the general formula I according to claim 1.
Are identical, respectively = NR ² -SO ₃ ^- X ⁺ is meant to and D and n a divalent residue of which is defined as in claim 1, except that in the residues A and B , R ²
Is ethylene or propylene and X ⁺ is hydrogen ion H ⁺ or, as in claim 1, Li ¹⁺ , Na ¹⁺ , K
¹⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Mn ²⁺ , Cu ²⁺ , Ni ²⁺ , Cd ²⁺ , Co ²⁺ , Zn
^Equivalent weight of the group consisting of ²⁺ , Fe ²⁺ , Al ³⁺ , Cr ³⁺ and Fe ³⁺ (M
^{m +} / m metal cation or ammonium) - ion N ⁺ R ³
R ⁴ R ⁵ R ⁶ wherein the substituents R ³ , R ⁴ and R ⁵ of the quaternary nitrogen atom are each independently of the other hydrogen atom or a hydroxyalkyl group having 2 to 3 carbon atoms and R ⁶ is It is one of the groups in the group of alkyl having 1 to 30 carbon atoms, alkenyl having 1 to 30 carbon atoms, hydroxyalkyl having 2 to 3 carbon atoms, and cycloalkyl having 5 to 6 carbon atoms. Item 1. A sulfonic acid group-containing perylene compound according to Item 1. 3. In the general formula I according to claim 1, A is --O--.
Or = a bivalent residue of NR ^1, B is = NR ² -SO ₃ ^- mean X ⁺ divalent residue and D and n are defined as in claim 1, provided that In the above residues A and B, R ¹ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms, or is unsubstituted or is a chlorine atom, a sulfo group, a bromine atom, a methyl group, an ethyl group, methoxy- and / or A phenyl group which may be substituted with an ethoxy group,
R ² is an ethylene- or propylene group and X ⁺ is a hydrogen ion H ⁺ or, as in claim 1, Li ¹⁺ , N
a ¹⁺ , K ¹⁺ , Mg ²⁺ , Ca ²⁺ , Sr ²⁺ , Ba ²⁺ , Mn ²⁺ , Cu ²⁺ , Ni ²⁺ , Cd ²⁺ , Co
²⁺ , Zn ²⁺ , Fe ²⁺ , Al ³⁺ , Cr ³⁺ or Fe ³⁺ equivalent amount (M ^{m +} / m) of metal cation or ammonium-ion N ⁺ R ³ R ⁴ R ⁵ R ⁶ with the substituents R ³ and R on the quaternary nitrogen atom
⁴ and R ⁵ are each independently a hydrogen atom or a hydroxyalkyl group having 2 to 3 carbon atoms and R ⁶
Is one of the groups from the group of alkyl having 1 to 30 carbon atoms, alkenyl having 1 to 30 carbon atoms, hydroxyalkyl having 2 to 3 carbon atoms or cycloalkyl having 5 to 6 carbon atoms, The sulfonic acid group-containing perylene compound according to claim 1. Wherein in the general formula I according to any one of claims 1 to 3, A is -O- or = NR ¹ or _{= N-CH 2 -CH 2 -SO} 3 - X
A ⁺ divalent residue, B is _{= N-CH 2 -CH 2 -SO} 3 - X + in a bivalent residue and n is a number equal to 0, provided that the residues A and In B, R ¹ is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and X ⁺ is a cation H ⁺ or Ca.
²⁺ / 2 or ammonium - an ion N ⁺ H ₃ R ^6, when the
The sulfonic acid group-containing perylene compound according to claim 1, wherein R ⁶ is defined as in 1 or 2 above. 5. A process for preparing a sulfonic acid group-containing perylene compound of general formula I according to claim 1, wherein perylene-
3,4,9,10-Tetracarboxylic acid-monoanhydride-monoalkali metal salt, perylene-3,4,9,10-tetracarboxylic acid-monoanhydride-monoimide or perylene-3,4,9,10 A tetracarboxylic acid-dianhydride having the general formula II H ₂ NR ₂ —SO ₃ ^— X ⁺ (II) [wherein R ₂ and X ⁺ have the meaning given in claim 1]. ] The sulfonic acid group-containing primary aliphatic amine represented by the following, and the aqueous solution, especially under alkaline pH conditions, at a temperature within the range of 50 ° C to 180 ° C, the above-mentioned method. 6. A process for preparing a mono- and di-sulfonic acid group-containing perylene compound of general formula I according to claim 1, wherein perylene-3,4,9,10-tetracarboxylic acid-monoanhydride-monoalkali. The metal salt, perylene-3,4,9,10-tetracarboxylic acid-monoanhydride-monoimide or perylene-3,4,9,10-tetracarboxylic acid-dianhydride can be represented by the general formula II H ₂ NR ₂ -SO ₃ ^- X ⁺ (II) [wherein R ₂ and X ⁺ have the meanings defined in claim 1. ] In a high boiling point inert organic solvent with a sulfonic acid group-containing primary aliphatic amine represented by
Process as described above, characterized by reacting in the range of 230 ° C., optionally in the presence of a catalyst. 7. A pigment dispersant for preparing a pigment preparation, which consists essentially of a perylene compound containing sulfonic acid groups of the general formula I according to claim 1. 8. A perylene compound of formula V